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Chemoselective Transesterification of Methyl (Meth)acrylates Catalyzed by Sodium(I) or Magnesium(II) Aryloxides
| Title: | Chemoselective Transesterification of Methyl (Meth)acrylates Catalyzed by Sodium(I) or Magnesium(II) Aryloxides |
| Authors: | Ng, Jie Qi Browse this author | | Arima, Hiro Browse this author | | Mochizuki, Takuya Browse this author | | Toh, Kohei Browse this author | | Matsui, Kai Browse this author | | Ratanasak, Manussada Browse this author | | Hasegawa, Jun-Ya Browse this author →KAKEN DB | | Hatano, Manabu Browse this author | | Ishihara, Kazuaki Browse this author |
| Keywords: | acrylate | | aryloxide | | BHT | | chemoselectivity | | DFT calculations | | magnesium | | sodium | | transesterification |
| Issue Date: | 1-Jan-2021 |
| Publisher: | American Chemical Society |
| Journal Title: | ACS catalysis |
| Volume: | 11 |
| Issue: | 1 |
| Start Page: | 199 |
| End Page: | 207 |
| Publisher DOI: | 10.1021/acscatal.0c04217 |
| Abstract: | A highly chemoselective transesterification of methyl (meth)acrylates catalyzed by sterically demanding 2,6-di-tert-butyl-4-methylphenol-derived NaOAr or Mg(OAr)(2) was developed. The desired transesterification proceeded without the undesired Michael additions under mild reaction conditions at 25 degrees C, and various primary and secondary alcohols, diols, triol, and tetraol on a scale of up to 10 mmol could provide the corresponding functionalized acrylates in high yields. Transition states were proposed based on monomeric and dimeric active species, and computational density functional theory calculations strongly supported high chemoselectivity to minimize undesired Michael additions. |
| Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS catalysis, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acscatal.0c04217 . |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/83756 |
| Appears in Collections: | 触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 長谷川 淳也
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